Playing Philadelphia
by Vera Cobb
Summary: WC Fields said he'd rather be in Philadelphia. Lit fans know that Rory should be there too, but considering that Fields also said 'A man's got to believe in something; I believe I’ll have another drink...' maybe Philly isn't such a good idea...
1. Drinking in Philly

**Drinking in Philly**

Rory Gilmore was drunk.

It didn't happen often. As much as her Mother had extolled the virtues of alcohol as a social lubricant, Rory had always been too responsible to really give in to it. Even when she'd been dating Logan Huntzberger, who could be hooked up to alcohol on an IV drip and still want a scotch, she'd rarely joined him. Correction – she couldn't join him, because someone had to be the designated driver. And that had been fine with Rory, for the most part. She liked to be in control.

She wasn't in control right now.

The world was spinning, very bright, very colourful. For some reason she thought it should be pretty, but actually, it was just making her nauseous. Her mind tried to analyse the situation. Why am I nauseous? It was just a few drinks. She tried to focus her gaze on the glass in front of her. Just one glass...or maybe there were two there. Hard to tell with the beer goggles on. But either way that's not enough to make me drunk! Even Miss Patty's Founder's Day punch isn't that potent.

But she hadn't been drinking anything as innocuous as Founder's Day punch and as the bartender approached and cleared the one glass in front of her, she realised that maybe she hadn't just had one or two drinks. She tried to glare at the bartender, angry with him for not cutting her off earlier. He didn't notice. She sighed heavily and turned herself slowly on her stool, trying to focus her vision enough to find the bar's exit.

Great! I have to get home. Visions of the Stars Hollow gazebo swam in her mind and she could picture her mom's jeep. It'd be nice to curl up in the back seat right now. Her legs hit the floor of the bar and she was pleased to find herself still upright. Gotta get to the jeep. But she had scarcely staggered more than three feet, her hands clutching at a table, before she realised that the jeep wasn't here. She wasn't in Stars Hollow. Where was she? Suddenly confused she collapsed back down into a seat at the table. Homeless. Was she homeless? No I'm not homeless. I just don't have a home. I have a ho-ho. No that's silly. A home…a holiday home? No! A hotel. I have a hotel. But what's it called? Not the Dragonfly. That's an Inn. But I live in an Inn! The world spun again as she dropped her head to the table, still confused.

'It's a nice table, huh?'

A voice broke into her consciousness, distracting her from her thoughts. She raised her head slowly to see a man's face grinning back at her. At least she thought it was a man. It could just as easily have been a monkey.

'Monkeys don't talk,' she corrected herself aloud.

The face looked surprised, but apparently wasn't too bothered about logic to be confused. 'That's true. Even in the circus, I've never seen a monkey talk.'

Rory was confused though. 'What?'

The face got back on topic. 'You sat at my table.'

Rory straightened up, looking around her as if astonished. 'Oh! I'm sorry. It's just that, I don't know where I live.'

'Well I'm pretty certain you don't live here. Not that I'm bothered. It's not like it's really my table. I just use it to drink at.'

Rory fought really hard to act sober and carry on a conversation. 'It's a nice table. Why are you drinking?'

'I'm not anymore. I'm waiting for my legs to start working again so I can go home.'

'Oh,' Rory nodded. 'I don't know where my home is.'

Yeah, you said that.' The face apparently wasn't quite as drunk as Rory. 'You look familiar. Do I know you?'

Rory started to shake her head, but instantly regretted it. 'No. I don't live here.'

The face smirked, though Rory was unaware. 'Yeah, I think that's been established.' He started to stand, slowly, his hands resting on the edge of the table to support his weight. 'Hey! Look at this! I'm functional!' He took a cautious step forward. 'I'm walking!'

Rory didn't look impressed. 'I've been doing that for years. My problem, is that I don't-'

'Know where you live. I know.' The face rolled his eyes. 'Well, hey, if you can walk and I can walk and I have a home, why don't you come with me?'

Rory blinked, trying to process the idea. She didn't have anywhere else to go.

'Come on! I don't live far away. And hey, you're hot, I'm…quite hot. It's a great idea.'

This was why Rory didn't like getting drunk. Drunken people did stupid, crazy things. They forgot who they were. They forgot where they lived. Anything could happen to them. They were vulnerable and all too susceptible to suggestion. They went home with strangers. They had bad, awkward, drunken sex and woke up feeling like crap.

But this night, Rory Gilmore _was _drunk.

She wrapped her arm around the man with the face as they supported each other to the door.

'Where do you live then?'

'Just around the block, above a book store.'

**A/N: 'Surprise!' 'No, not really,' you think. 'Ha!' I scoff. 'Just you wait!' **

**Just to clarify - this world is exactly the same as the world we knew on the show. Everything that happened there, happened here. That might make some of this seem a bit strange, but if you stick around, the next chapter should clear things up for you. Please review! This is the first proper story format story I've posted, so I'm a tad nervous.**


	2. Hungover in Philly

**Hung-Over in Philly  
**

Rory Gilmore was hung-over.

She knew this, even before she opened her eyes. She could tell, by the way the light outside the window was already blinding her through her eyelids. She could tell by the way her mouth tasted and the way her head throbbed. She could tell by the way the bed sheets rubbed at her bare skin - Bare skin?

Despite the pounding in her head, Rory sat bolt up right, wide-eyed. As her mind screamed at the light, her eyes took in the strange bedroom and the unfamiliar view from the window. She didn't need to look down to know she was naked. She could see her clothes strewn across the floor of the room. Not wanting to look, but knowing she had to, she turned her head slowly to her left, looking down at the figure sleeping next to her. He lay on his stomach, his head face down, buried into his pillow.

Who the hell is that? Where am I? Rory sat, frozen in the bed, clutching the sheets in front of her chest and breathing only slightly, so afraid was she of waking her...one night stand. Oh my God!! I had a one night stand! I don't even know his name! Do I? She bit her lip nervously, desperately trying to process the events from the night before. There had been alcohol. A lot of alcohol. Where had she been?

_Rory walked nervously into the bar, frowning at the faded sign above the door. Really? He wants to meet me here? It certainly wasn't her first choice of venue for a first date. But then, she wasn't all that familiar with Philadelphia and she figured her date wasn't either. The Holiday Inn is on Arch Street. The Constitution Centre is on Arch Street. Truncheon Books is on Locust Street. _Jess_ is on Locust Street._

Way to go Gilmore; start thinking about an ex when you're on a date. With Guy. She remembered the charming, mop haired reporter asking her out a few days ago. It'd been six months since Logan Huntzberger had unceremoniously left her at her Yale graduation. Guy seemed harmless enough.

_The place was quiet. Guy wasn't there. Great. She took a seat at the bar, trying not to feel pathetic for being alone. Do I order a drink? Well I can't sit here and just eat their peanuts._

As the memories came slowly back, Rory mentally kicked herself. Really shouldn't have ordered a drink. At least, not a martini. So much for trying to be cool and sophisticated. She remembered more clearly now. She was already finishing her second drink when her phone had beeped with a message.

_'Sorry. Met old friend. Will have to reschedule.'_

_She'd been stood up. Rory gaped at her phone in shock for a moment, before closing it angrily. He messages me now? Twenty minutes after he was supposed to be here? She didn't know whether to just be angry or be humiliated. She settled for both, which resulted in her ordering another drink. _

She couldn't remember what her third drink had been. She winced and closed her eyes, embarrassed. Stupid, stupid Rory!

_The drink was good. She couldn't really taste it, but it stopped the feelings of humiliation. She smiled at the bartender and asked for more nuts, which he happily provided. The pretty tipsy girl at the bar was a precious commodity in joints like this._

Rory felt nauseous as she remembered the bartender offering her another drink on the house. So I got well and truly fahsnickered. But how did I end up with… She turned her head again to look at the sleeping lump beside her. He'd shifted a little and she could see his face clearer now. He looks familiar. Of course he looks familiar. You had sex with him last night! Sensible Rory was scolding herself, but logical Rory knew she wouldn't find him familiar if that was all she'd done. Her gaze traveled around the room again, taking in the stacks of papers on the desk, the books and the – photos! She stared, transfixed by a picture hung on the wall beside the bed. Three guys stood in front of a building she knew. One of the three locations in Philly that she could name.

'Oh my God!' She leapt out of the bed as if she'd been electrocuted, pulling the blanket with her.

_She wrapped her arm around the man with the face as they supported each other to the door._

_'Where do you live then?'_

_'Just around the block, above a book store.'_

As if on cue, a fist rapped on the door and a voice that was far too familiar called out: 'Matt? Are you up? I'm making coffee and Chris is asking for breakfast. You want some?'

Rory just stood, staring wide-eyed at Matt as he sat up groaning, obviously feeling the effects of his own hangover.

'Yeah man. I'm coming,' he flopped back onto the bed and dropped an arm over his face, feeling the light burning into his brain. 'And make it hangover food!'

Rory knew she should be relieved that the voice at the door hadn't walked in, but honestly, she was far too busy being terrified. I slept with Matt!

He'd closed his eyes again, apparently oblivious to her presence. Suddenly realising that maybe she could escape she stepped furtively towards her pile of clothes, but jumped back violently when Matt sat up and stared at her.

'Oh! Hello!'

She tried to keep her face hidden and moved again towards her clothes.

'Um, hi. Sorry, I'm just going to leave.'

Matt watched her awkwardly for a second, evidently trying to piece the situation together the same way Rory had. His mind worked quicker while hung over.

'Wow. Crazy night huh?'

'That's one way of putting it.' She kept the bed sheet around her shoulders as she slipped her jeans on, not bothering to find her underwear.

'You don't do this a lot do you?' Rory ignored him and Matt smirked as he watched her trying to locate her shirt. 'It's on the chair.'

Rory looked at the chair he pointed to, seeing her shirt thrown over the back. She still refused to make eye contact.

'Thanks. And no, I don't do this a lot. Or at all. Ever.' She could live without a bra. The shirt went on as quickly as the sheet fell away from her shoulders. Matt was still staring at her.

'You really do look familiar.'

Finally dressed, Rory at last felt capable of looking at Matt. 'We've met before,' she muttered, trying to smooth her hair back into a pony tail.

'We have? I knew it! When?'

Rory was about to speak when there was another rap on the door and it swung open.

'Coffee delivery! Get your ass out of bed before-' Jess stopped dead in his tracks, staring at Rory and blinking furiously. Rory just stared back, body tensed and mouth frozen open.

'Huh.'

**A/N: Well done to the reviewers who figured it out. So far as I've seen, this scenario hasn't been done before, so I hope you all enjoy it. Let me know what you want to see next.**

**Toodlepip.**

**~VC**


	3. The Morning After in Philly

**A/N: Muchos gracias for the reviews last chapter. They make me grin. I love that I managed to surprise people. Enjoy this!**

**~VC  
**

**The Morning After in Philly**

Rory Gilmore's world was spinning.

She was even willing to lay down money that it was spinning more now than it had last night. Oh god…last night…

'Rory?'

She saw Jess staring at her, looking more confused than she thought anyone ever had.

'Jess.' She could see him trying to make sense of what he was seeing. His gaze finally moved from her to Matt, who was still sprawled naked under a thin cotton sheet. His eyes grew bigger.

'Wow. Alcohol really makes you do the wacky.' Ooh, bad choice of words. 'I should go.'

Jess seemed to snap out of his stupor suddenly and his gaze swung back to stare Rory full in the face. She froze mid stride, just two feet from the door. Damn.

'What the hell happened?' Jess's voice was tight. He doesn't really need me to explain it does he? But he did. Somehow she knew he needed her to just tell him. He needed confirmation that this was real.

Okay, fine, I can do this. It's easy to explain. But though she started to speak a few times, the words just wouldn't come.

Matt suddenly spoke up. 'Holy hell and fuck me blind. You guys know each other! Oh! You're the girl! I knew you looked familiar. You came to our open house and broke his heart...'Cos you were his…Oh shit.' He sat up straighter in his bed and looked at Jess. 'I'm really sorry man.'

Rory quickly nodded her agreement. 'Me too. This is really weird and awkward and I'm so sorry. I didn't know what I was doing. I was drunk and the bartender was – well he was evil – coz' he had the drinks and the nuts and he didn't stop me. Coz' I was there alone and I was pathetic and I didn't know what I was doing. I didn't mean to…do this.'

Jess's gaze fixed on her as if he was trying to shut out the rest of the world (and the sight of Matt in bed). 'Well were they good nuts at least?'

Rory's mind immediately blanked at the comment, going to the dirty place. She knew Jess hadn't meant it, but before she could stop herself, the obligatory 'Dirty!' had slipped out.

Needless to say, Jess looked slightly horrified at this reference to his friend's nuts. Rory wanted to kick herself; repeatedly. Okay, turning sensors on.

Jess tried to play cool. 'There's a bathroom down the hall if you want to use it. I'll make more coffee.'

He was gone before Rory could speak again. She looked guiltily over at Matt.

'Wow, Rory, I'm sorry.'

She shrugged helplessly. 'Me too. We were both idiots.'

'Oh, that's nothing new. My village calls at least once a week asking if I'm coming back,' he added musingly, 'They always seem really happy that I'm not.'

Rory smiled at him, weakly.

'I guess you're not usually the idiot type?'

She was about to confirm his statement when she suddenly started to think; about playing mother to Logan and babysitter to Colin and Finn; to fighting with Lorelai and dropping out of Yale, stealing a yacht…to sleeping with a married man. She got so caught up rewinding the past few years in her mind that she didn't realise how much time had passed until Matt started to pull on his clothes.

'Oh – sorry.' She turned away, embarrassed. Matt just smirked.

'It's okay. You zoned out for a bit. And hey, this is nothing you haven't seen before.'

Rory felt her face flush with humiliation. Matt grimaced.

'Sorry. Didn't mean to embarrass you.' He finished pulling on his jeans and walked around to face her. 'Hey? It's okay. I know this isn't normal for you.'

Rory shook her head. 'Actually, it is.' Seeing Matt's surprised face, she rushed on, trying to clarify. 'Well, no, this isn't. This definitely isn't. But I've definitely done plenty of other idiotic things.'

'Really?' Matt looked skeptical.

She looked at him ruefully. 'Ever stolen a yacht?' His eyes seemed to double in size as he looked at her, probably trying to decide if she was being serious. Rory stood up. 'Didn't think so. So, um, it's okay if I use your bathroom?'

Matt nodded. 'Sure. Two doors down, on the left.'

She heard Matt muttering as she walked out.

'Man he's gonna' yell at me so much once you're gone.'

********************************************************************

Rory! And Matt! Rory in Philly. With Matt.

Jess was barreling around the kitchen washing dishes, drying dishes, rewashing the dishes that he'd just dried; wiping the counter and moving the coffee machine backwards and forwards as if finding a perfect location for it would make everything better. Chris had left him alone and gone downstairs. The poor guy didn't know what was going on, but the way Jess was acting made him certain that it was better to be Not Here.

Jess had to admit, if he wasn't so emotionally involved, he'd find it slightly funny. He kind of wished he could have seen good, sensible Rory last night, drunk enough to go home with Matt. Matt! It had only been two days ago that a heartbroken Matt had emphatically declared that he was giving up on women for good. Jess snorted. Of course, no one had believed him, but Jess had never expected to find him with Rory. His Rory. Scratch that. She wasn't his. But then she sure as hell wasn't Matt's and yet, Matt had…

'Don't go there,' he muttered to himself. 'Just be nice, give her coffee and let her leave. Then we can murder Matt.'

'Please don't murder me.' Matt wondered into the kitchen, hesitantly.

Jess didn't look up from the thrice washed plate he was drying. 'Hey.'

'I'm really sorry Jess.' He picked up one of the mugs of coffee from the counter.

Jess nodded. 'You didn't know.'

'Fuck no! I had no idea who she was or…anything. And I mean it when I say that's it; no more women for me. Ever!'

Jess rolled his eyes. 'Sure. From now on we will call you Matt the Eunuch.'

'Sounds fair. She's in the bathroom. I'll go downstairs.' Matt left, taking his coffee with him and Jess was glad for the solitude. Unfortunately, it didn't last long.

'Hey.'

He hadn't heard her come in. She stood by the door, watching him nervously. He froze at the counter, looking at her across the small space. Play it cool Mariano.

'Hey. Feel better?'

'Not exactly.'

'Not a good night then?'

Her face flushed and she bit her lip. 'I don't remember most of it.'

'Alcohol will do that to you.' He looked around awkwardly, trying to find something to keep him busy. 'So, I made coffee.' He moved over to pour her some, unconsciously using the biggest mug they had.

'Thanks.'

'He cheat on you again?' He didn't realise he'd said the words out loud until he saw Rory's reaction.

'What?'

'The blonde dick from Yale? Did he get carried away with his secretary? His maid? His hairdresser?'

Rory looked pissed. 'God, Jess! No!'

Jess shrugged. 'Well the last time you came here looking for that,' he gestured his hand towards Matt's bedroom, 'you were out for revenge.'

'I didn't come here looking for anything. I didn't even mean to come here. I went to a bar. Got stood up. Drank too much and then completely humiliated myself.' Her voice grew shrill as she tried to defend herself.

'Oh,' say something idiot. 'So, did _he_ stand you up?' No! Don't say that!

'No.' Her reply was soft.

Jess tried to keep his face impassive. 'So, you and him?'

'We broke up, after Yale.'

Why did he feel smug all of a sudden? He shouldn't care either way. 'Sorry.'

She shrugged. 'It's okay. I'm fine. It was my choice. Kind of. I didn't want to marry him.'

'Oh, wow. He wanted to marry you?'

'Yep. But apparently not enough to wait for me.'

'What an idiot.' Once again the words came out before Jess could sensor them.

Rory looked up, his words apparently surprising her as well. A soft smile played at her lips. Jess, meanwhile was mentally punching himself. He tried to steer the conversation back to current topics.

'So you drank yourself stupid in a bar and came home with Matt?' Perfect delivery. There was a hint of careless amusement in his voice that he was very proud of.

'I didn't know who he was. Wow, that makes it even worse doesn't it?'

Jess chuckled finally, shaking his head. 'Oh no. Going home with Matt willingly would be worse.'

Rory grinned at him suddenly and they both visibly started to relax. Jess tried not to think about how beautiful she still was.

A frown crossed her face suddenly. 'Hey Jess? Do you have some asprin?'

He decided to adopt the persona of Teasing Jess. 'Maybe. I don't know if I should give it to you though. This new drunken-floozy-Rory might try to snort it or OD on it. I don't want you pulling a Penny Lane on me! You know what your mom would do to me, right? Never mind Luke!'

She smiled then, for real. 'Jess, Penny Lane didn't OD on asprin!'

He looked smug. 'So you were paying attention.'

'After watching _Almost Famous_ seven million times, something was bound to sink in. Now please, give me drugs!'

Jess feigned uncertainty.

'I swear on Ernest Hemingway that I will use the asprin responsibly.'

He scoffed. 'That means nothing. You hate Hemingway.'

'Kate Hudson?'

A snort this time. Rory sighed.

'Fine. I swear on Mark Twain.'

Jess nodded. 'He's dead, but I'll take it.' He got the asprin from a drawer and handed it to her with a glass of water. Rory took it gratefully.

'Thanks Jess.'

'Anytime.'

Rory raised her eyebrows. Jess backpedaled.

'I didn't mean that. This was a one time deal. I do not want to find you in Matt's room ever again!'

'Suits me.'

********************************************************************************

Rory was surprised at how easy it was to just fall back into their casual old banter. After a while the awkwardness of the morning wake up seemed to be forgotten and they were teasing each other, making lewd comments and arguing about the varying merits of certain authors, just like they had back in High School. They sat in the lounge room, on opposite ends of the couch and she filled Jess in on her current job as an online reporter for the Barack Obama campaign and he told her stories about the numerous artistic personalities he had to deal with during his work at Truncheon.

'So don't you have work you should be doing?' Jess finally asked.

'Don't you?' she countered.

'Day off.'

'Oh.'

'So?'

'Yes I have work to do, but it won't get done today. Can't you feel how much my head is pounding?'

He smirked at her, eyebrows raised. 'Nope.'

'Oh yeah. Of course.' She leaned her head back into the couch and closed her eyes. It seemed suddenly supremely comfy. 'I like this couch,' her voice was getting drowsy. 'I promise not to sleep with Matt again, but please can I sleep with your couch?'

Jess scoffed. 'You can, but don't blame me if you wake up and find the coffee table assaulting you. They've been going steady for a year now.'

She smiled as she curled herself up tighter. 'Okay.'

She heard him stand and pick up the coffee mugs. His footsteps padded towards the kitchen.

He was being so nice to her. He always was, when he wasn't being an ass. Back when they were dating there had been those awkward moments when she'd been hanging out with Dean and he'd found out after the fact. He never yelled or stomped or pounded his chest in rage like Dean often had when the situation had been reversed; he'd just ask her to give him a heads up next time. For someone who avoided human interaction as much as he did, he was remarkably understanding.

He'd been polite to Logan, even when Logan was a complete jerk. She almost wished it had been the old, angry Jess that had come to the bar with them in Hartford. That Jess would have kicked Logan's ass into the next galaxy.

Rory smiled at that thought and the pictures it created behind her eyelids, as she snuggled into the couch cushion.

***********************************************************************************

Jess knew Rory hadn't noticed his return. He perched himself on the coffee table in front of her, watching as she hugged the couch cushion, grinning like a Cheshire cat.

'Wow, you and that cushion are getting pretty close. Should I give you some alone time?'

Her eyes flipped open and he could see her embarrassment. 'Um, ha, I was reminiscing.'

He raised his eyebrows, curiously and watched as she pulled herself back upright, tugging the pillow onto her lap in the process.

'About the time me and Jake the Cushion went to the Winter Carnival? I really wasn't expecting him to go; really wasn't his scene. But when it came to the crunch, he cracked! I guess he couldn't resist my charms. I won him a bear on the Bottle Toss. Good night.'

'Huh.'

'Huh?'

'I'm sorry, my memory must be going. I could have sworn that _I_ took you to the Winter Carnival.'

She shrugged, looking down at the cushion and hiding a small smile.

'Well whoever it was, it was a really good night.'

'It was.' There was a pause before Jess leaned forward, whispering softly, 'You know, I still have the bear.'

Rory's jaw dropped as she grinned. Her hand flung out, pointing at Jess.

'You kept it? Really?'

Jess shifted, clearing his throat and staring at his shoes. 'Guess I'm just a hoarder.'

'You kept your Rory Bear!'

He was grinning when he looked back up at her and he reached over to slap her knee. 'You can't mock me about that! I saw your room at your grandparent's house, remember?'

'Jess has a teddy bear, Jess has a teddy bear,' she sing-songed, ignoring Jess, and choosing instead, to revel in this new revelation.

He sighed, shaking his head. He knew he'd unleashed a monster and so tried desperately to change the topic. 'Bought a new book the other day. It had pages in it; words; a few seriously hard core sentences; and you should have seen the apostrophes!' It didn't work.

'And to think I was going to give that bear to Clara.'

Fine. Can't distract the monster. Tackle it head on.

'So why were you thinking about the Carnival?' Bingo. Her face changed, from mocking to nervous in point zero two seconds.

'Well Jake the Cushion brought it up.'

'Jake the Cushion wasn't there.' He knew his voice was getting husky. He knew where he was leading this conversation; straight towards Heartbreak and Despair. He knew he should stop, but somehow, when faced with Rory, Jess Mariano's head never did quite function properly.

She was chewing her lip, a clear sign that he was making her nervous.

'I was just, remembering, how nice you were.' Her voice was low, tense.

'Huh. I thought I was just a no good hoodlum.'

'Oh you were,' she looked at him, smiling for a moment. 'But you were nice to me as well.'

'I screwed up a lot.'

'So did I; I just did it later on.'

'True. Luke told me about your Grand Theft Boato.'

She groaned and dropped her head into her hand. 'Gah! Don't remind me.'

'So when you look at it, given the stealing and the dropping out of school and the drunken-floozy behaviour, I'm starting to think maybe _you'd_ make a better town hoodlum.'

Her head rose and she stared at him for a moment, as if considering something.

Don't kiss her! Don't kiss her! He could hear his heart pounding the words, though he really didn't want to listen to them. Presently, she spoke.

'Aren't hoodlums supposed to sneak out of places and go sit on benches? Stare at their shoes?'

He couldn't believe she remembered that. He grinned and stood up.

'Delinquent Gilmore, I believe you're right. But they also have to steal a book first.'

She smiled, digging a hand into the couch cushion behind her and retrieving a very unhealthy looking copy of _Doctor Sax. _

'Done.'

'Hey, I was wondering where that went! I fell asleep reading it so many times I just gave up.'

'Well now I'm stealing it, so you don't have to read it anymore.' She stood, pushing the book into the waist of her pants.

'So, do you know where I can find a good bench around here?'

He had to fight _really_ hard to keep a huge grin from splitting his face. He succeeded.

'I might know of a couple.' He grabbed his jacket from the arm of a recliner and headed for the door. Rory followed.


	4. Realisations in Philly

**Realisations in Philly**

Rory Gilmore was realising something.

She was tired and she was still hung over. She knew she was supposed to be following Jess. She had taken a good half dozen steps away from the couch, heading to the door. She just couldn't seem to get much further. Jess was already through the door.

Keep going, she told herself. It'll be good! She really did want to go out. She was enjoying her time with Jess, and getting out of the apartment where she'd had a drunken rendezvous with one of his best friends could only make things better.

But the thing about drunken rendezvous is that they don't always leave you feeling particularly wonderful. Right now, Rory felt like crap. There was no way she was making it to the door. She was about to throw herself back in the direction of the couch and her new lover, Jake the Cushion, when she felt the unpleasant churning in her stomach that could only mean one thing.

It was time to start running.

**********************************************************************

Jess walked back into the apartment frowning. He was sure Rory had been following him, but unless she'd developed herself some sort of Wonder Woman cloaking device (and he doubted it; Rory had never been one for the sciences), she wasn't with him now.

Hearing the retching coming from the bathroom he rolled his eyes. Of course; there was no way she'd be wondering around Philly today. He shrugged off his coat and went to the kitchen to start cooking.

He'd just thrown out the first pancake (why was Luke the only person that didn't always destroy the first attempt?), when Rory padded back into the kitchen.

'You made the right choice.'

Rory's brow furrowed as she stared at him, not comprehending his meaning.

'Staying in? Doctor Sax would have only made you more nauseous anyways.'

'Oh.' Rory leaned against the wall, wearily. 'Sorry Jess. I really did want to go out.'

'Well you'll just have to make do with pancakes,' he consoled, adding a handful of choc-chips to the pancake batter. Rory smiled.

'They're choc-chip pancakes!'

Jess smirked, but didn't look up. 'Looks like it.'

'You remembered!'

'Well your freaky Gilmore dining habits leave an impression.'

She moved closer to him, watching as he lifted the pan off the heat and flipped the pancake over. 'Whoa! When did you get so good at that?'

'You can't hang around Luke for two years and not pick up some stuff.'

She cocked her head thoughtfully. 'Well I've known Luke since I was ten and I sure as hell can't do that.'

'You never watched him cook,' he replied, sliding the pancake from the pan. 'And trust me, it's better that you don't ever try. If you must make a pancake, stick to using a spatula.'

'You have no faith in me!'

'Rory!' His tone was warning as he saw her sliding into the space before the stove.

How did she do that? He'd only stepped away from the stove for three seconds to grab a plate! She was grinning at him impishly. 'Should I crack an egg? Put more butter in? Should I turn up the gas? What do I do now?'

'Now you step away from the stove, hands in the air. Do not touch the knobs. Do not touch the spoons. Do not touch the pan.'

'Please?' Her eyes grew big and she stuck out her lower lip, but Jess remained immune.

'No. Freaking. Way. Now get your ass over here and eat this pancake.' He held out the pancake he'd just served and rolled his eyes as Rory immediately abandoned her place at the stove and accepted his bribe, seating herself at a stool against the counter.

'This is good,' she said between mouthfuls. 'I'll need second helpings.'

He shook his head, knowing he shouldn't be astonished and yet still mildly impressed by Rory's iron stomach.

'You can have as many pancakes as you like, so long as I never see them again. I am _not_ holding your hair for you if you throw up again.'

'I wouldn't ask you to.'

'Good. Because vomit makes me vomit.'

'Um, Jess? Can you not talk about vomit while I'm eating?'

He chuckled at the look on her face. Finally, it seemed, there was something that made her stomach queasy.

Six pancakes and two cups of coffee later, he consented to let Rory leave her stool and the two cleaned the kitchen together, although Jess still insisted that he be the one to wash the stove.

'You're so territorial!' Rory teased, splashing him with her wet hands.

'No, this is just being careful.' He threw the dirty cloth back into the sink, smiling in satisfaction as it splashed water over Rory. She squealed.

'Ah! You low-down-'

'Amazing guy who made you breakfast and coffee and didn't complain when you tried to make out with his couch?'

Rory looked guilty for a second and he was sure he heard her sigh. 'Not where I was going, but, yeah, I suppose that's accurate.' Her face grew flushed as she looked down, fingering the hem of her shirt.

'Hey, Rory?' His voice sounded tentative, even to him. 'It's okay.'

She didn't look up, but shook her head. 'No it's not. It's humiliating.'

He just stood awkwardly, not quite knowing what to say now. She was right. It wasn't okay, but he couldn't say that. Rory looked up at him, sadly.

'I'm sorry Jess.'

His mind seemed to freeze suddenly. He was back in Matt's bedroom, watching her tying up her ponytail, mouth gaped open and Matt's naked ass in the bed next to her. Was she really sorry? Could she really comprehend how much that had killed him? Or was she just apologising to make herself feel better? Or because it was the polite thing to do? Everyone knew that Rory Gilmore was nothing, if not polite.

**********************************************************************

Idiot! Rory scolded herself, as she watched Jess's face change. She desperately scanned her vocabulary for a word better than 'sorry.' It sounded so trite and pathetic and it didn't come close to saying what she wanted to say. What do I want to say? Sorry I had a one night stand with your best friend? Sorry I've made you play nice all morning? Sorry I came back to Philly again? And what had Matt said this morning? '_You came to our open house and broke his heart.' _Was that true? She had never let herself believe that Jess really loved her, telling herself it was all just another Crazy Jess Gesture. He couldn't love her, not now and not four years ago.

_She stood in the cold and yelled at him. _

_'No word, nothing!' She wanted to hurt him like he'd hurt her. 'So talk. What do you have to say to me? '_

_He stared at her, his brown eyes vulnerable, terrified. 'I love you.'_

She'd had to convince herself then that it wasn't true. Things were simpler that way. Jess leaving her with no word, to go to California, had hurt her more than she could let on to anyone. If she'd believed him, when he told her he loved her it would have broken her heart again, because she'd have to admit to herself that she'd loved him as well.

She shook her head, trying to get rid of her thoughts and focus back on reality. Jess was still staring at her, obviously as stuck for words as she was. Run, Gilmore, run! She could hear Coward Rory chanting in the back of her mind. It seemed the best plan. All she would achieve hanging around here was to get her heart broken again, or, (though she only entertained this thought for a second), hurt Jess again.

'I should go.'

She dropped her tea towel by the sink and strode quickly from the kitchen, gathering her bag from the table. She was at the door before Jess had recovered enough to follow her. She paused, hand on the door knob and turned to look at him.

'So…'

He waited a moment before responding. 'So,' he echoed, causing another silence that might have lasted indefinitely if it weren't for the ringing of her cell phone.

She answered it automatically.

'Rory Gilmore.'

'Hi Rory!' The voice on the other end of the line stopped talking, as if waiting for her to respond.

'Hi…?' She spoke slowly, not sure who it was.

'How are you?' Man she hated that question. It was such a stupid thing to ask, especially on the phone and especially when you hadn't identified yourself yet. She decided in that moment that if she ever decided to get into politics, she was going to petition for a screening process to stop idiots getting phones. 'Hello?'

Oops. She hadn't answered her caller. 'I'm sorry, who is this?'

'It's Guy!' the voice on the line said, with an unmistakable hint of 'Duh!' in his tone.

'Oh. Guy. Of course.' What to say next? Why are you calling me you little freak? Why didn't you call yesterday, instead of letting me sit drinking, alone in a strange bar? Okay, maybe not. She still had to work with this guy. 'What's up?' But that didn't mean she couldn't be a little snippy. 'Did you forget how to send a text message?' She saw Jess watching her curiously and rolled her eyes at him.

Guy laughed nervously. 'Sorry about that. I ran into an old friend from high school. We used to do track together. You know what it's like, you start reminiscing and time just flies by.'

'Hmm,' she grunted, sounding bored.

Guy hurried on. 'Anyway I was calling to check about the function tonight. You're going, right?'

'The Press function?' Shit. She'd forgotten about that. It was some fancy mixer thing some paper or other was throwing for the Campaign trail reporters. Officially, attendance was optional, but in reality, not showing up would be frowned upon by organisers and reporters alike. 'Yeah, I'm going.'

'Great. Shall we make it a date?'

'A what?' Rory cried. Was he really asking her out again?

'A date? We'll go together, seeing as last night didn't work out.'

And whose fault was that, she thought maliciously. But how to respond now? 'Actually, last night worked out really well for me.'

'It did?' Guy sounded confused.

'Yeah. I ran into an old friend as well.'

'Oh. A guy?' Rory felt a sick sort of pleasure at hearing the nervous uncertainty in his voice.

'Yes, a guy.' That's it Gilmore: insert sword and twist!

'Oh. So…You're bringing _him_ to the function?'

'Yep.'

'Right. Okay then. Bad luck for me I guess.' His disappointment was palpable. And twist sword in other direction! Rory smirked for a moment. 'Well I'll see you both tonight then.'

'Yeah, you will see us both tonight.' Wait - both? Shit. What had she just said?! She quickly replayed the conversation in her head. And remove sword and stab directly into own big mouth. Oh no. I didn't say that. No no no no no.

'Bye.' Guy had hung up before Rory could say anything else.

She just stood there, phone still pressed to her ear before she closed her eyes and groaned, head falling back on her shoulders. 'No…'

'Rory?' There was a definite probing tone to Jess's voice as he startled her out of her imaginary self-mutilation.

'Jess?' She mimicked, not lifting her head up.

'Did you just agree to go somewhere with an old friend you met last night?'

'Yes.' Her voice was barely a squeak.

'Huh. So either, you and Matt have seen more of each other than I realised, or you met someone else last night before you met Matt. Did you run into Luke?'

She didn't lift her head, but shook it slowly, dropping her phone away from her ear. 'Dean?' he pushed, a different tone in his voice. She kept moving her head. 'Oh no. Please tell me you're not taking Kirk to a press function?!'

Her head lifted at that and her eyes flew open. 'What would Kirk be doing in Philadelphia? I don't think Kirk even knows that there's a world beyond Woodbury.'

Jess chuckled. 'Good point. So?'

'So?'

'Who's this mysterious 'old friend' you ran into?'

'He's imaginary,' she mumbled, stuffing her phone back into her bag.

Jess nodded. 'Cool.' He stuck his head forward and dropped his voice. 'I have imaginary friends too.'

Rory quirked her eyebrows, a small smile playing on her lips. 'Plural friends? Wow Jess. That's just sad…and a bit desperate,' she teased. 'I only have the one.'

**********************************************************************

Jess pretended to look insulted. 'I'm sad? I'm not the one who has to use my imaginary friend as an imaginary date! What's his name?'

'David Bowie.'

'Huh. Well I guess it's a more common name than I realised.'

Rory poked her tongue out at him, then shook her head, ruefully. 'I just didn't want to go to an event with the guy that stood me up twenty four hours earlier. I know, I'm an idiot. It's like it's my new trademark or something these days. They should make a drinking game out of it.'

'One shot whenever Rory acts stupid?'

'Or says something stupid. Or does someone stupid,' she added, rolling her eyes at the grimace on Jess's face. 'And there I go again. Take a drink. Ugh! Why is this so hard?'

'You want my advice?'

Rory nodded, looking at him hopefully.

'One you leave Philly just call it an alcohol induced one night stand and don't thing about it ever again.'

Rory's face dropped in disappointment. 'That isn't the part that I'm finding hard.'

'Oh?'

She gestured her arms about her. 'This! This is the hard part. You having to see, _that_,' she gestured to Matt's room, 'and you being nice to me and us joking around like nothing has happened, only we both know that something did and it's not just an elephant in the room, it's an elephant with all of his circus buddies, starting a conga line.' She was still gesturing, pointing to something in front of her that Jess could only imagine to be a hallucinatory elephant.

He tried to interrupt. 'Rory just forget-'

'So we joke and we make fun and we reminisce and hey, Guy was right! You can completely get caught up in the reminiscing, only then the elephant stands in front of you, shaking his maracas, or the monkey trips over and it's kind of cute and funny but really it's not nice and it's mean and I feel mean and horrible and I honestly never meant to hurt you Jess.' She stopped gesturing, shoving both hands into her pockets. Her voice dropped a little, but she kept her eyes focused on his. 'Not this time and really not last time. I just didn't want to believe that what you said in Stars Hollow might be true, coz' it would hurt too much, so I was stupid and ignored it and then when I came here last time it was like this and maybe the elephant was here even then.' She broke eye contact for a moment, blinking furiously at the ground. 'I think he was. He was smaller, like Dumbo, you know? But he was here and I ignored him and let you kiss me and then I took off and was Matt right?'

Now Jess was blinking furiously, trying desperately to keep up with her rant. 'Right about what?'

Rory released a shaky breath. 'He said I came to your open house and broke your heart.'

He frowned. Did she really want to go down this road? 'You know W.C. Fields?' The question obviously threw her off but she nodded slowly.

'He said "If at first you don't succeed try, try again. Then quit. There's no use in being a damn fool about it."'

'Oh…what?'

He sighed heavily, running a hand through his hair. 'I mean, don't make me go there again Rory. I don't want to be the fool anymore.'

She finally seemed to realise what he was saying. 'It was true then,' she breathed. 'All the time.'

'It was true,' he confirmed, turning away, not trusting himself to look at her. There was a tense silence, but Jess didn't dare wonder what she was thinking. Had she really convinced herself that he hadn't loved her? Was he really that bad at showing his feelings? Admittedly, he hadn't exactly been the perfect boyfriend. Fuck knows, he hadn't been like Dearly Devoted Dean, but in his opinion, Rory had always seemed suffocated by that guy. She seemed so independent. He'd never realised how much she'd relied on him.

Ah jeez! Now I'm back to blaming myself for stuff that happened years ago. What's Rory thinking? No! Don't go there. You've answered her question. Just leave it at that.

Finally, she spoke. 'You know, Fields said you should always carry a small flagon of whisky, in case of snake bite.'

Jess turned back to her, eyebrows raised.

'He also said you should always carry a small snake.' She gave him a small smile and he furrowed his brow, looking at her curiously.

'I don't get it. Are you the snake or the whisky?'

She shook her head. 'It's not a metaphor. I just mean…do you do everything Fields says?'

It took a moment for her meaning to sink in. When it did, he shoved his hands in the pockets of his jeans and rocked back on his heels, staring at the ground. 'So…Is Bowie really going to take you to this thing tonight?' He tilted his head, watching her from the corner of his eye.

She smiled. 'Do you have a better idea?'

**A/N: Thanks for the reviews folks. I have no idea if I'm getting Jess's reaction right. How would a person really be in this situation? Yeah, it would suck, but how much do you have to blame on the alcohol? At some point you just have to suck it up and move on, or you'd spend ages being all angsty and boring. I think...maybe. Anyways, please let me know what you think of this chapter. **

**~VC**

**PS - WC Fields is hilarious.  
**


	5. Fools in Philly

**Fools in Philly****  
**

Rory Gilmore was a fool.

Having finally made her way back to her hotel (the Holiday Inn on Arch Street; next time she goes on a date, she's going to tattoo her address to her arm), Rory collapsed on the edge of her bed and stared blankly at her open suitcase, trying to wrap her head around the mess she'd created.

So far, since arriving in Philadelphia, she'd agreed to a date with a guy she didn't really know; been stood up; drunk herself into a state of complete idiocy; had a one night stand with a stranger who'd turned out to be not quite as stranger-ly as she'd first thought; been reunited with her ex; stirred up a whole bunch of confusing and not always pleasant memories and now…now she'd somehow wrangled aforementioned ex into accompanying her to a press function, to cover up a lie she'd told to the guy who had previously stood her up.

Rory tried to come up with a simple way to sum it all up, but just kept coming back to the word 'mess' and various variations of it. In happier news, her headache seemed to have moved on and Jess's choc-chip pancakes had settled her stomach. She glanced at her watch, noting the three hours she had left before the function and tried to figure out what the hell she could do to pass the time.

Ten minutes later she abandoned her book. _The Woman in White_ wasn't distracting enough. Twenty minutes after that, she turned off the television without even being aware of what she'd been staring at (because she'd been staring; not watching). Another ten minutes and the room service menu was discarded and she took her iPod out, placing it on the bed and blasting music through the super loud headphones. If anyone had asked however, she wouldn't be able to tell them what song was playing. All she could think of was her mess. And Jess.

Her recent realisations about what he felt for her were absolutely playing havoc with her brain. Okay, maybe talking to each other through random quotes hadn't been the most direct way to deal with things, but she thought she understood what he was telling her. _'If at first you don't succeed try, try again. Then quit. There's no use in being a damn fool about it...I mean, don't make me go there again Rory. I don't want to be the fool anymore.'_ Surely that implied that going there was still an option? She nodded her head slowly. It did. The more she replayed the scene in her mind, the more she was certain what he meant. He'd tried so many times to win her, without success (though to be fair, most of his techniques left something to be desired), he was afraid to put his heart on the line again. He didn't want to be the fool. But that didn't mean he wasn't.

She felt herself blush, remembering her own somewhat convoluted response. Had she really told him to ignore Fields advice? Coz' she was ninety nine percent sure that that implied something on her part. In crazy-Rory speak, she'd asked him to try for her, again. She could barely remember formulating the response. He'd just opened up to her and her damn heart had started pounding like the rhythm section of a Royal Crown Revue song (She Walks On Fire – that was the song – turbulent, erratic and dizzying). Then her mouth had opened, the words had fallen out and he'd accepted it as easily as he always did. He'd offered himself up like a lamb for the slaughter. Because she'd asked; and if her heartbeat had been anything to go by, she'd wanted him to.

'Stupid foolish heartbeat,' she muttered suddenly to herself, unconscious of Buddy Holly singing to her from the iPod about the issues he had with his own heartbeat. 'Damn heartbeat tricked me.' But if she was going to be honest (and Rory Gilmore liked to believe she always was) he'd always made her heart skip like crazy. Gah! And so began the battle between the foolish voices in her foolish head and the foolish words that kept falling from her mouth.

Eight minutes later she was startled out of her internal and external debate by the ringing of her phone. Jess, she thought. He's calling to cancel. He's been hauled off to the big house for killing Matt. She frowned. No. Don't go there. That would turn this mess into a whole other kind of disaster.

'Hello?'

'How was it?' Oh god, how did she know already?

'It?' Rory squeaked.

'The date? Good? Bad? Ugly?' Rory shook her head, reassuring herself that her mother couldn't possibly know about it. 'Oh no. Don't tell me it was ugly. I thought you already knew the guy?'

'The date was a non-event Mom.'

'Oh?' Lorelai was surprised.

'He met up with an old friend yesterday and…cancelled.' No need to mention that he hadn't cancelled until twenty minutes after the date was supposed to start.

'Aw, hun. Shucks,' her mom's tone was sympathetic. 'So what'd you do instead?'

Of course, leaving out information doesn't always make things easier. Rory sighed.

'Well I just...hung out?' Even Rory could hear the lie in her own voice. To her mom, she knew, it would be like a foghorn.

'Rory? What happened?'

She checked her watch and sighed again, settling back against the pillows on the bed. Still two hours to kill. She had time.

'I got drunk.'

At least this would be a distraction.

***********************************************

Jess narrowed his eyes at his reflection, taking in the blazer and white shirt he wore. The outfit was awfully similar to the one he'd had on two years ago at the Truncheon open house. And no, it wasn't weird that he remembered the clothing choices for that day. There were a number of photographs of the event scattered around both the apartment and the work space downstairs.

So should he change it? Wear something else? Something that wouldn't remind him (and her?) of that day? His gaze fell on the bulging laundry hamper in the corner. Nope. There weren't many other options.

And he was too far in this for a wardrobe change to matter now. With Rory, he was always too far in. She'd broken his heart (smashed, shattered, pulverized), but he knew he'd caused more than his share of pain in their early years. (Year - They never did get enough time).

He hoped he understood the situation this time. Hoped they were both on the same wavelength. She had asked for this, hadn't she? She'd told him to disregard Fields. Not to worry about being a fool. She'd asked him to try again, hadn't she?

Don't question it. Don't over analyse. Forget about the hard stuff.

He tried to tell himself to just keep it simple. Help Rory by being a good fake date and enjoy spending time with one of the few people in the world that he cared about. With any luck, the evening would go smoothly, whatever the ending might be. The ending…why did the thought of the ending terrify him? (Any ending – good, bad, amazing, disastrous – all the options were terrifying).

Jess sank his head to his knees as he sat on the bed and pulled on his shoes. Admit it punk; you know how it ends in your dreams. The same way all your dreams end...the way reality never does.

'I instigated it.'

He sat up sharply, eyes flying to Matt who leaned awkwardly against the door frame. 'If I remember things right, she couldn't remember where her home was.' There was a pause and Matt cocked his head to the side, before he added musingly 'And I think she thought I was a monkey.'

Jess's eyebrows quirked up at this information. Matt looked back at him, shaking his head. 'Forget I said that.'

'Gladly,' Jess said dryly, standing up and going back to the mirror. He wasn't really expecting to see anything different. His shoes weren't going to magically change his outfit, or make him feel braver. He just needed something to keep him busy. Awkward conversations with pals were never his forte.

'I'm sorry Jess. I just wanted to say that. I know I fucked up.'

Jess shrugged nonchalantly. 'I know. But you didn't plan it.' Matt relaxed against the door frame as Jess added in a low voice. 'I just didn't want to see her again. At least, not like that.' He glanced at Matt's reflection in the mirror. Their eyes met and he saw him nod.

'I swear, from now on I'm a eunuch.'

'Yeah, I believe you,' Jess said with a smirk as he turned around. His tone was lighter. 'Now if you'll excuse me, I've got to go. I have a hot date with your organ grinder.' Jess was already striding from the room, but cringed inwardly as he realised the double meaning in what he'd just said…it seemed the sensors still weren't working.

**********************************************************

'Hey.'

'Hey.' She stood in front of him, awkwardly, her palms pushed against her thighs and her fingers playing with the fabric of her blue cocktail dress. He knew she was nervous. Weirdly, her nervousness relaxed him. At least he knew they had something in common. 'Thank you so much for doing this.'

For doing what? Being your fake date or playing the fool? 'It's okay. You look nice.' He tried to smile reassuringly and leaned in, placing his hand on her elbow as he gently kissed her cheek.

It seemed to work. Her stance relaxed and a warm glow appeared on her cheeks. Huh. Seemed he still had an affect on her. He smirked.

'So, I guess we should go in,' she said, gesturing to the set of double oak doors behind them.

He nodded. 'Okay.'

The function room was large and airy with buffet tables set along one of the walls. As Jess took in the people milling about, he was relieved to find that however much he had second guessed his outfit, it seemed to fit in with this crowd. It seemed reporter types were pretty cool. Rory seemed to relax even more, now that they were in side. After scanning the room she smiled up at him and held out her hand. 'Come on.'

He took it without question and let her lead him over to a makeshift bar area, where two girls stood surveying the beverages.

'Rory!' the blonde one cried as they approached, 'I don't know what I want! Tell me what I want! Meg is useless.'

Rory rolled her eyes at the girl who wasn't Meg. 'You want a beer. A Corona.'

Meg smiled. 'That's what I've been telling her but she thinks a beer will give the wrong impression. She wants to be sophisticated Cassie tonight.'

Rory sighed dramatically. 'We have this discussion every time. You like beer. Beer is good. Drinking anything just because you think it looks good is ridiculous.'

Cassie sighed in defeat. 'I like Corona,' she acknowledged quietly. 'Will you have one too?'

Jess eyed Rory curiously, watching with amusement as her face blanched. 'Actually, I think I'll stick to coffee tonight.' She turned to him, 'Jess, do you want a drink?'

'A Corona would be great.'

Meg grinned. 'See Cas! You won't be the only one drinking beer. It's all good.'

Cassie shook her head. 'It doesn't count. He's a guy. They can drink what they like.'

Meg wasn't to be outdone. 'Yeah, but Rory is drinking coffee and I'm drinking soda… Surely beer is better than that?'

This seemed to make up Cassie's mind and moments later the bartender handed over two Coronas, and a soda. Rory's coffee, it seemed, would have to be scavenged from elsewhere.

Drink debacle resolved, Meg and Cassie turned their attention to Jess. 'So, who are you?' Meg asked, eying him over her soda.

'Oh, sorry guys,' Rory quickly took over. 'This is Jess. Jess, this is Meg and Cassie. They're on the campaign trail with me, obviously. Jess works at a publishing house, here in Philly.'

Jess was surprised at how easy it was to fall into idle conversation. He still wasn't any kind of chatter-box, but he saw the smile on Rory's face as he strung together multiple sentences, explaining his work at Truncheon. If he were willing to admit it to himself, he might think she looked proud. But he realised suddenly that she also looked empty handed.

At the next lull in the conversation he looked at her, eyebrows raised. 'Hey, you want to go find your coffee?'

She grinned at him. 'Is Hemingway painful?'

He frowned at her in mock seriousness. 'Uh, I think what you meant to say was "Is Hemingway amazing?" Otherwise I'd have to assume you don't want coffee.'

Rory looked at him like he was nuts. 'Ha! I don't think so! I definitely want coffee, ergo, Hemingway is painful. Let's go.' Again, she grabbed his hand, waving goodbye to Meg and Cassie as she pulled him away, though he still protested.

A lap of the room later, Rory stood, shoulders slumped. There was no coffee to be found.

'This is ridiculous! We're journalists! Coffee is our number one food group. Why wouldn't they serve it?'

Jess had to admit, it was a little odd. There was a buffet table with an assortment of light snack type foods and there seemed to be plenty of alcohol. So where was the coffee? Finally he noticed a small alcove at the end of the tables that was completely deserted. This time he grabbed Rory's hand, pulling her along. 'Over here.'

Rory grinned as she stood in front of the secluded table, set with mugs and a coffee pot. 'You found it!'

'Yup.'

'My hero!' She set about pouring out her coffee. 'Thanks Sherlock. You averted another Rory-breakdown.'

He tilted his head, a smile curling one side of his mouth. 'Glad to be of service.' He watched as she gulped at the coffee. 'Is it any good?'

Again she gave him that are-you-nuts? look. 'God no. It's cold and weak and blah, but it's coffee! I love it.'

He chuckled, knowing better than to question her logic. 'Of course.' There was a pause, then 'Blah?'

She shrugged. 'Blah. It's an adjective for taste. Sweet, sour, salty, bitter, chocolate, blah.'

He smiled then, properly. 'Chocolate is an adjective?'

'Duh! Chocolate cake, chocolate biscuits, chocolate milk, chocolate ice-cream-'

'Okay I get the point. You win.'

She blinked at him, 'I didn't know it was a competition?'

He placed his hand on her back, steering her back out into the main crowd. 'Rory Gilmore, with you, everything is a competition.'

She looked intrigued by this idea, but the pair of them were soon swamped by her fellow reporters, so further discussion was put on hold. Jess played his part, again making friendly small talk. He knew Rory was enjoying this new side of him. Not that he had to say much; true to form, Rory was more than capable of speaking enough for ten people.

A barrage of people later, they were again walking alone. The crowd was starting to thin out as people left for their hotel rooms. Rory had her thinking face on. 'Everything with me is a competition?' she asked.

'Every conversation with you turns into a debate,' he clarified. 'So, yeah.'

She spun around so she was walking backwards as she looked at him with an impish grin. 'You're right. And in the great Hemingway debate, I win.' Childishly she poked her tongue out, then spun back away from him.

He was about to grab her arm so he could contradict her when a tall man stepped before them. Almost immediately, Jess was reminded of Dean, and as he gazed up at the goofy grinned, floppy haired person, he couldn't help the amused smirk that crossed his face. It was Dean 2.0.

'Rory! Hi!'

Rory stiffened immediately. 'Oh, hey Guy.' Ah, the absent date.

'I'm so glad to see you. I just wanted to apologise again for last night. I know I screwed up. Please let me make it up to you. You know I'll do anything for another chance. A movie? A book sale?' Ugh. Dean 2.0 might be even closer to the original version than he'd thought. He had the puppy dog eyes and the sincere desperation down pat. Jess half expected him to offer to build her a car next.

Rory however was laughing uncomfortably, her gaze flying behind her to Jess. 'Um…well-'

Instinctively, he stepped closer and wrapped an arm protectively around her waist. Dean 2.0 looked at him in surprise. 'Oh. Hi.'

For some reason Jess decided it was time for Hoodlum Jess to make an appearance. 'Hey,' he replied lazily.

'Uh, I'm Guy.'

'Huh.' Yep. He had officially regressed. Somehow he knew Rory was fighting to keep a straight face.

'I work on the campaign trail with Rory.'

He felt his stomach flip as she crossed her arm across her stomach and laced her fingers in his. Don't grin. Don't grin. Meanwhile poor Dean 2.0 just stood there, looking increasingly uncomfortable.

'Oh.' Jess wondered how long this could go on.

'Guy, this is Jess.' It seemed Rory was going to take pity on the poor fool, but then he saw that impish grin on her face again. 'Jess is my mono-syllabic coffee hero.' Okay, apparently Rory wasn't so compassionate these days. Don't grin. Don't grin.

He saw the utter confusion on Dean 2.0's face, followed by something that looked like embarrassment. 'Oh. Right. Okay.' And with that intelligent and clever response, the man was gone. Rory spun around, eyes sparkling and Jess finally allowed his grin to match hers.

'That was mean!' he said softly.

'That was payback!'

'Rory Gilmore, you've grown up.'

'And you grew back down,' she pointed out with a knowing smirk. 'That was brilliant. It felt like High School again,' her voice dropped and her face changed to a soft smile. 'I've missed old Jess.'

He was suddenly acutely aware of the fact that her fingers were still entwined with his and he found himself staring at them. There was only one thing he could respond with. 'Huh.'

'Jess?' her voice was breathy and tentative. He knew she was looking at their hands as well. Suddenly, he could feel her fingers trembling. Automatically his free hand reached out to grab hers and she stepped closer.

He tore his gaze away from their hands, looking at her face. 'Rory?'

Her eyes met his and she held his gaze as she spoke softly. 'I won't run away this time.'

Though the crowd was thinning, there was still plenty of chatter and noise in the room; people gossiped, laughed, flirted, clinked glasses…but for a short time, the space that Rory and Jess occupied was silent, save for the occasional gasp for air. Lips met, softly at first, but with increasing fervour. Their hands separated and Jess moved his to hold Rory's face, while she wrapped one arm around his waist and slid the other hand to the back of his head. She pulled herself in close to him and he heard her moan softly as their bodies pushed flush against each other. Tongues slipped through puffy lips, teasing, tracing and then dueling for dominance. His hands moved to mirror hers, one sliding around her back, pulling her still closer, while the other cradled the back of her head as they kissed each other senseless.

Screw the consequences. Jess Mariano would always be a fool for Rory Gilmore.


	6. Dizzy in Philly

**Dizzy in Philly****  
**

Rory Gilmore was dizzy.

Unlike her previous dizzy spells, this one was not brought on by the excessive consumption of alcohol. Oh no. This was a very different kind of dizzy; Jess's lips assaulted her own, his fingers pushed onto her skin and every nerve in her body screamed in ecstasy.

When they finally pulled away from each other, Rory's face was flushed red and her pupils were dilated. Her hands automatically slid back into Jess's. Looking at Jess, she noticed he was also sporting a very sexy Post-Kiss demeanour, though it didn't last very long.

'Rory Gilmore, you just kissed me!' His tone was surprisingly light and his smirk was settling back on his face.

'Uh, no! I believe you kissed me.'

'You kissed me back. Ergo, you kissed me.'

'Is that bad?' She mimicked his light tone, but inside her stomach was churning. Don't regret this! Don't regret this!

'Not so long as you don't run away now...'

Relaxing again, Rory leaned forward and kissed him softly, chastely. 'I'm not running.'

'Good.' Jess's voice had grown husky again and she contemplated the fact that he had been playing the light angle in order to cover his own uncertainties.

Half an hour later, Rory and Jess stood in front of her hotel room door. Both of their lips were swollen and Rory had an interesting blemish on the side of her throat that Jess had seemed particularly proud of leaving.

'So...'

'So...' Rory echoed Jess. What now? She couldn't invite him in. She knew what would happen if she did and then...Well if she did that she'd never leave. Not to mention the fact that she'd been with Matt only 24 hours earlier.

'When do you leave Philly?'

Rory looked down at the carpet, unconsciously squeezing Jess's hands. 'Tomorrow morning.'

She felt Jess release one of his hands, running his fingers softly along her arm. 'You gonna come back?'

To her horror, she felt tears burning her eyes and blinked furiously, willing herself not to cry and refusing to look up from the carpet.

'Rory?' He seemed to know what she was trying to do and without another word he wrapped his arm around her back and pulled her into his chest. Well that wasn't going to help! The second she felt her face press against his shirt the tears fell from her eyes and she hiccupped softly through her sobs. His hand rubbed through her hair tenderly and she could hear him murmuring softly. 'Shh, it's okay. Shhh.'

Suddenly the reality of her situation seemed to come back to her and her tears stopped as she pulled away . 'Ah! I'm so sorry Jess. This is ridiculous!'

'It is?' Jess was staring at her uncertainly and she could see the nervousness back in his face.

'Isn't it? Me...I mean...you were....and we only just...and now I'm acting like Ilsa Lund and that's just not cool.'

'Well of all the gin joints, in all the towns, in all the world you did just have to walk into Matt's,' Jess smiled wryly.

At this Rory giggled a little and a blush tinged her cheeks. 'Don't remind me.'

'I'm glad.'

'What?' she asked, surprised.

'We wouldn't be here now if you hadn't...if it hadn't happened...'

'That's very gracious of you Mister Mariano.'

Jess just shrugged nonchalantly. 'Yeah, well...that's me.' There was a moment of silence as they both stared at each other and Rory realised suddenly how incredibly comfortable she was with this and with Jess. She was calm. Not happy to be leaving, but she didn't feel all the years of hurt and confusion anymore.

A tiny smile curved her mouth. 'The elephant is gone now, isn't it?'

Jess couldn't hold back his smile. 'Yeah. He's gone.'

Still smiling, Rory leaned forward, wrapping her arms around Jess's neck, and kissed him hard.

'I'm not gonna get lucky tonight am I?' Jess muttered into her ear with a light chuckle.

Rory stepped back and slapped him lightly on the arm. 'Jess!' She was laughing though.

He just grinned. 'It's okay. Once you leave I'll go out with Matthew and steal a yacht or something.'

She choked on the laughter in her throat. 'You are so mean!' She raised her hand to slap him again.

'Yeah, but you love me anyway.'

Her laughter and her hand froze.

The world seemed to be going in slow motion. Jess wished he could sink into the carpet and disappear. For a guy who didn't say much, his words were certainly getting him into trouble lately.

Rory looked like a rabbit caught in the headlights, just staring blankly at him and blinking rather stupidly and her hand still raised as if about to slap him.

He hadn't meant it to be some huge assumption that she loved him. He'd just been joking...Great! Now he was going to scare her off. Just freaking brilliant.

'I do.' Rory's voice sounded amazed. Slightly astonished. Jess looked at her enquiringly. She met his gaze steadily as she repeated herself, 'I do love you.' This time the statement was made more assuredly, though her face still told that this was only a recent admission to herself.

Not that any of that mattered to Jess. He grabbed her raised hand in his as he launched himself forward, pushing her back to the wall and pressing his mouth to hers. This kiss was hot, desperate and brutal. He wanted to claim her, completely. She loved him! The last time he'd heard her say something even close to that was during a one sided phone conversation in California. '_I think I may have loved you, but I just need to let it go...'_ This was so much better.

Her hands clung to the back of his head, her fingers curling into his hair as she arched her back, pushing herself into him. Jess felt the shivers running down his spine. He wasn't sure how the hotel room door opened. Logically he figured Rory must have done it, since she had the key, but he had no idea when or how.

Once inside the room he pushed her back up to the wall again. He pushed himself against her so tightly he was sure he couldn't go any further, but with a heady groan from Rory he suddenly found her arched against him still more.

His hands slid to her thighs, rubbing down through the material of her dress and then wrapping around the backs of her legs as he hoisted her into his arms. Her head rolled back and he took the opportunity to suckle on her neck again, feeling a warm rush in his stomach as he heard the noises that elicited.

Finally collapsing with her onto the bed, he shuddered as her fingers trailed along his skin and her hands pulled at his shirt, lifting it over his head. She breathed heavily, staring at his torso and then gripped his shoulders, pulling him back down to her and catching his lips as she moaned his name.

His hands returned to her legs, sliding her dress up, but pausing as he reached her waist.

He pulled back so that he was kneeling over her on the bed, her legs trapped between his. He focused on her face and his smile matched hers as they gazed at each other. For a moment he wondered if this was really happening. How many times had he dreamt this, or some variation of it? If it was a dream, he was certain he never wanted to wake up.

But he felt her nails pinching at his arm and then heard her voice again, repeating her words from earlier. 'Jess? I love you.' This time there was no hesitation or surprise in her voice or her face. She meant it. Absolutely. And he knew it was real; in his dreams, he'd never let himself hear those words.

He slid her dress over her head and then her hands pulled at his belt and undid his pants. He lay on his side, pulling her into his arms and kissed her neck softly as his fingers played over the soft skin at her sides. He could feel the goose bumps and felt crazily proud of himself for having put them there.

When the rest of their clothing came off he finally found himself plunging inside her. He felt her teeth biting into his shoulder and was sure that in the whole entire history of the world, no one had ever felt as wonderful as he did right now.

She'd been dizzy earlier, but this was just ridiculous. Every kiss, every caress and every look from Jess made her head spin, her nerves buzz and her stomach clench. Sometimes the world seemed to be moving in slow motion; seconds lasted for hours and a kiss could last a hundred years. A thought tripped through the back of her brain that she could write a book as long as _War and Peace_ about all the incredible sensations she experienced in that short space of time; the way her voice choked in her throat when she felt his breath on her nipple, or the way that her toes curled as his fingers played her. But then something would shift and suddenly things seemed to be moving at the speed of the Concord and she had to cling to him, to keep herself from hurtling off into space.

When she finally did let go, she decided space was somewhere she definitely liked. They lay next to each other, both sprawled across the bed, only just touching. Eventually her breathing started to steady and she could hear his doing the same. She turned on her side and tilted her head up to look at him. She wanted to giggle when she saw his hair mussed all over the place – apparently his hair gel wasn't designed to stand up to Rory Gilmore.

He saw her looking at him and rolled over to face her, taking her hand in his as he did so. 'That was unplanned.'

Rory smirked. 'You weren't supposed to get lucky tonight. That wasn't in the script.'

Jess shrugged. 'When have I ever followed the script?'

Rory paused as she opened her mouth, obviously struggling for something to say. Eventually she yawned and then shrugged as well. 'I'm glad you don't.'

'Yeah?'

'Yeah,' her voice was soft and she was smiling as she closed her eyes.

She heard Jess's voice gently intruding on her trip to Dreamland. 'Rory? When the campaign is over...tell me you're going to come back.'

Valiantly fighting off sleep, she nodded her head slowly and squeezed his hand. 'I am,' she was barely aware of him squeezing her hand in return, but before sleep completely took her she managed to mumble, 'I'd rather be in Philadelphia.'

She wasn't coherent enough to see the smile on Jess's face as he rolled onto his back and pulled her into his arms.

******************************

_And that's all folks. Thanks for reading this. Admittedly, I wasn't going to end it quite here, but all of a sudden it seemed that continuing it would only result in covering ground already trodden many times. This was my first time writing the more intimate stuff as well, so I hope I did it justice._

_Cheers,_

_VC  
_


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